Composition for an organic electronic device and organic electronic device using the same

ABSTRACT

Provided are a composition for an organic electronic device and an organic electronic device using the same. The composition includes a first host compound represented by the following Formula (I) and a second host compound represented by the following Formula (II). 
     
       
         
         
             
             
         
       
         
         
           
             wherein Y is a single bond, O or S; Z 1  to Z 3  are each CH or adjacent two of Z 1  to Z 3  are joined together to form an aryl ring or a heteroaryl ring; two of X 1  to X 3  are each a nitrogen atom, the other of X 1  to X 3  is CH or a nitrogen atom; Q 1  and Q 2  are each CH or Q 1  and Q 2  are joined together to form an aryl ring.

CROSS-REFERENCE TO RELATED APPLICATION

Pursuant to 35 U.S.C. § 119(e), this application claims the benefits ofthe priority to U.S. Provisional Patent Application No. 62/680,625,filed Jun. 5, 2018. The contents of the prior application areincorporated herein by its entirety.

BACKGROUND OF THE INVENTION 1. Field of the Invention

The present invention relates to a composition for an organic electronicdevice and an organic electronic device using the same, moreparticularly to a composition that includes two host compounds for anemission layer and an organic electronic device using the same.

2. Description of the Prior Arts

With the advance of technology, various organic electronic devices thatmake use of organic materials have been energetically developed.Examples of the organic electronic devices include organic lightemitting devices (OLEDs), organic phototransistors, organic photovoltaiccells, and organic photodetectors.

OLED was initially invented and proposed by Eastman Kodak Companythrough a vacuum evaporation method. Dr. Ching W. Tang and StevenVanSlyke of Kodak Company deposited an electron transport material suchas tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq₃) on atransparent indium tin oxide glass (abbreviated as ITO glass) formedwith a hole transport layer of organic aromatic diamine thereon, andsubsequently deposited a metal electrode onto an electron transportlayer to complete the fabrication of the OLED. OLEDs have attracted lotsof attention due to their numerous advantages, such as fast responsespeed, light weight, compactness, wide viewing angle, high brightness,higher contrast ratio, no need of backlight, and low power consumption.However, the OLEDs still have the problems such as low efficiency.

To overcome the problem of low efficiency, one of the approaches is tointerpose some interlayers between the cathode and the anode. Withreference to FIG. 1, a modified OLED 1 may have a structure of asubstrate 11, an anode 12, a hole injection layer 13 (abbreviated asHIL), a hole transport layer 14 (abbreviated as HTL), an emission layer15 (abbreviated as EL), an electron transport layer 16 (abbreviated asETL), an electron injection layer 17 (abbreviated as EIL), and a cathode18 stacked in sequence. When a voltage is applied between the anode 12and the cathode 18, the holes injected from the anode 12 move to the ELvia HIL and HTL and the electrons injected from the cathode 18 move tothe EL via EIL and ETL. Recombination of the electrons and the holesoccurs in the EL to generate excitons, thereby emitting a light when theexcitons decay from excited state to ground state.

Another approach is to adopt1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi) as a hostmaterial of the EL. However, even using the foresaid host material ofthe EL, the driving voltage and the current efficiency of OLEDs stillneed to be improved.

Therefore, the present invention provides a novel composition tomitigate or obviate the problems in the prior art.

SUMMARY OF THE INVENTION

An objective of the present invention is to provide a composition for anorganic electronic device.

Another objective of the present invention is to provide an organicelectronic device using the composition, so as to reduce the drivingvoltage and improve the current efficiency of the organic electronicdevice.

To achieve the foresaid objectives, the present invention provides acomposition for an organic electronic device which comprises a firsthost compound and a second host compound.

The first host compound is represented by the following Formula (I):

In Formula (I), Y is a single bond, an oxygen atom or a sulfur atom.

In Formula (I), Z¹ to Z³ are each independently CH, adjacent two of Z¹to Z³ in Formula (I) are joined together to form an aryl ring and aremaining one of Z¹ to Z³ is CH, or adjacent two of Z¹ to Z³ in Formula(I) are joined together to form a heteroaryl ring containing at leastone furan group or at least one thiophene group and the remaining one ofZ¹ to Z³ is CH.

In Formula (I), two of X¹ to X³ are each independently a nitrogen atom,and the other of X¹ to X³ is CH or a nitrogen atom.

In Formula (I), L′, L¹ and L² are each independently an arylene grouphaving 6 to 18 ring carbon atoms. L′, L¹ and L² are the same ordifferent.

In Formula (I), n′, n1 and n2 are each independently an integer from 0to 2. n′, n1 and n2 are the same or different.

In Formula (I), G¹ and G² are each independently an aryl group having 6to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbonatoms, an arylthioxy group having 6 to 18 ring carbon atoms, or aheteroaryl group containing a N, O, or S atom and having 3 to 30 ringcarbon atoms. G¹ and G² are the same or different.

The second host compound is represented by the following Formula (II):

In Formula (II), L³ is an arylene group having 6 to 18 ring carbonatoms.

In Formula (II), n3 is an integer from 0 to 2.

In Formula (II), Q¹ and Q² are each independently CH, or Q¹ and Q² arejoined together to form an aryl ring.

In Formula (II), G⁴ and G⁵ are each independently an aryl group having 6to 18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbonatoms, an arylthioxy group having 6 to 18 ring carbon atoms, or aheteroaryl group containing a N, O, or S atom and having 3 to 30 ringcarbon atoms.

By means of containing the first host compound including a triazinemoiety or, which is a pyrimidine moiety, and the second host compoundwhose main skeleton includes at least two carbazole moieties, the firstand second host compounds of the composition can form an exciplex. Thatis, the first host compound is as an acceptor compound for the exciplex,and the second host compound is as a donor compound for the exciplex.Therefore, the composition for an organic electronic device can reducethe driving voltage and improve the current efficiency of the organicelectronic device using the same.

In accordance with the present invention, the first host compound may berepresented by the following Formula (I′):

wherein Y, Z¹ to Z³, X¹ to X³, L¹, L², n1, n2, G¹ and G² are as statedabove.

In the case that Y is a single bond and all of Z¹ to Z³ are each a (CH),and the first host compound may be, for example, represented by

In the case that Y is a single bond, adjacent two of Z¹ to Z³ are joinedtogether to form a heteroaryl ring containing at least one furan groupand the remaining one of Z¹ to Z³ is CH, the first host compound may be,for example, represented by

For Formulae (I-II) and (I-III), Z¹ is CH and Z² and Z³ are joinedtogether to form one furan group.

For Formulae (I-VI) and (I-VII), Z¹ and Z² are joined together to formone furan group and Z³ is CH.

In the case that Y is a single bond, adjacent two of Z¹ to Z³ are joinedtogether to form a heteroaryl ring containing at least one thiophenegroup and the remaining one of Z¹ to Z³ is CH, the first host compoundmay be, for example, represented by

For Formulae (I-IV) and (I-V), Z¹ is CH and Z² and Z³ are joinedtogether to form one thiophene group.

For Formulae (I-VIII) and (I-IX), Z¹ and Z² are joined together to formone thiophene group and Z³ is CH.

In the case that Y is an oxygen atom and Z¹ to Z³ are each independentlyCH, or in the case that Y is an oxygen atom and adjacent two of Z¹ to Z³are joined together to form an aryl ring and the remaining one of Z¹ toZ³ is CH, and the first host compound may be, for example, representedby

For Formula (I-X), all of Z¹ to Z³ are each a (CH).

For Formula (I-XI), Z¹ is CH and Z² and Z³ are joined together to formone naphthyl group.

For Formula (I-XII), Z¹ and Z² are joined together to form one naphthylgroup and Z³ is CH.

In the case that Y is a sulfur atom and Z¹ to Z³ are each independentlyCH, or in the case that Y is a sulfur atom and adjacent two of Z¹ to Z³are joined together to form an aryl ring and the remaining one of Z¹ toZ³ is CH, the first host compound may be, for example, represented by

For Formula (I-XIII), all of Z¹ to Z³ are each a (CH).

For Formula (I-XIV), Z¹ is CH and Z² and Z³ are joined together to formone naphthyl group.

For Formula (I-XV), Z¹ and Z² are joined together to form one naphthylgroup and Z³ is CH.

Preferably, L′, L¹ and L² are each independently a phenylene group.

Preferably, n′ is the integer 0 or 1.

Preferably, n1 and n2 are each independently the integer 0 or 1. In somecases, both n1 and n2 are the integer 0. In some other cases, both n1and n2 are the integer 1. In some other cases, n1 is the integer 1 andn2 is the integer 0. In some other cases, n1 is 0 and n2 is the integer1.

Specifically, G¹ and G² may be a specific aromatic substitution. Thespecific aromatic substitution may be selected from the group consistingof:

where X is O, S, or

wherein * is the bonding site;

p is an integer from 1 to 5, m is an integer from 1 to 4, n is aninteger from 1 to 3; and

A¹ to A³ are each independently selected from the group consisting of: ahydrogen atom, a deuterium atom, a halo group, a cyano group, a nitrogroup, an alkyl group having 1 to 6 carbon atoms, an alkenyl grouphaving 2 to 6 carbon atoms, and an alkynyl group having 2 to 6 carbonatoms.

Specifically, the group of (L¹)_(n1)-G¹ and (L²)_(n2)-G² of the firsthost compound represented by Formula (I) or Formula (I′) may be eachindependently selected from the group consisting of:

Preferably, the aryl group having 6 to 18 ring carbon atoms representedby G¹ or G² may be selected from the group consisting of:

More preferably, the aryl group having 6 to 18 ring carbon atomsrepresented by G¹ or G² may be selected from the group consisting of: aphenyl group, a naphthyl group and a 3, 5-diphenylphenyl group.

Preferably, the heteroaryl group containing a N, O, or S atom and having3 to 30 ring carbon atoms represented by G¹ or G² may be selected fromthe group consisting of:

Preferably, the group of

of the first host compound represented by Formula (I) or Formula (I′)may be selected from the group consisting of:

For example, the first host compound may be selected from the groupconsisting of:

For example, the first host compound may be any one of the followingcompound:

Or, for example, the first host compound may be any one of the followingcompound:

The first host material also may be any one of the compounds disclosedin U.S. Patent Application Publications No. 2017/0213978 A1, No.2017/0213970 A1, No. 2018/0159044 A1, and No. 2018/0155312 A1.

Preferably, the second host compound may be represented by any one ofthe following Formulae (II-I) to (II-III):

wherein W¹ and W² are each independently a methyl group, an ethyl group,a propyl group, a butyl group or a phenyl group.

For Formula (II-I), both Q¹ and Q² are each a (CH).

For Formulae (II-II) and (II-III), Q¹ and Q² are joined together to forman aryl ring.

Preferably, L³ is a phenylene group.

Preferably, n3 is an integer 0 or 1.

Specifically, G⁴ and G⁵ may be a specific aromatic substitution. Thespecific aromatic substitution may be selected from the group consistingof:

where X′ is O, S, or

wherein * is the bonding site;

p′ is an integer from 1 to 5, m′ is an integer from 1 to 4, and n′ is aninteger from 1 to 3; and

A⁴ to A⁶ are each independently selected from the group consisting of: ahydrogen atom, a deuterium atom, a halo group, a cyano group, a nitrogroup, an alkyl group having 1 to 6 carbon atoms, an alkenyl grouphaving 2 to 6 carbon atoms, and an alkynyl group having 2 to 6 carbonatoms.

Preferably, the aryl group having 6 to 18 ring carbon atoms representedby G⁴ or G⁵ may be selected from the group consisting of: a phenylgroup, a biphenylyl group, and a naphthyl group.

More preferably, G⁴ and G⁵ are each independently selected from thegroup consisting of:

For example, the second host compound may be selected from the groupconsisting of:

In accordance with the present invention, a weight ratio of the firstand second host compounds ranges from 3:7 to 7:3. Preferably, the weightratio of the first and second host compounds ranges from 4:6 to 6:4. Insome cases, the weight ratio of the first and second host compoundsranges from 4.5:5.5 to 5.5:4.5.

In this specification, said “arylene group having 6 to 18 ring carbonatoms” denoted by L′, L¹, L², or L³ may be an unsubstituted arylenegroup having 6 to 18 ring carbon atoms or an arylene group having 6 to18 ring carbon atoms substituted with at least one substituent exceptfor a hydrogen atom. The at least one substituent on the arylene groupmay be selected from the group consisting of: a deuterium atom, a halogroup, a cyano group, a nitro group, an alkyl group having 1 to 12carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynylgroup having 2 to 12 carbon atoms, an alkoxy group having 1 to 12 carbonatoms.

In this specification, said “aryl group” may be an unsubstituted arylgroup or an aryl group substituted with at least one substituent exceptfor a hydrogen atom; said “heteroaryl group” may be an unsubstitutedheteroaryl group or a heteroaryl group substituted with at least onesubstituent except for a hydrogen atom. Similarly, said “aryloxy group”may be an unsubstituted aryloxy group or an aryloxy group substitutedwith at least one substituent except for a hydrogen atom; said“arylthioxy” may be an unsubstituted arylthioxy group or an arylthioxygroup substituted with at least one substituent except for a hydrogenatom.

The at least one substituent on the aryl group may be selected from thegroup consisting of: a deuterium atom, a halo group, a cyano group, anitro group, an alkyl group having 1 to 12 carbon atoms, an alkenylgroup having 2 to 12 carbon atoms, an alkynyl group having 2 to 12carbon atoms, and an alkoxy group having 1 to 12 carbon atoms. Thesubstituent on the heteroaryl group, aryloxy group, or arylthioxy groupmay be similar to any one of the at least one substituent on the arylgroup as stated above.

In this specification, said “alkyl group” may be an unsubstituted alkylgroup or an alkyl group substituted with at least one substituent exceptfor a hydrogen atom, said “alkenyl group” may be an unsubstitutedalkenyl group or an alkenyl group substituted with at least onesubstituent except for a hydrogen atom, and said “alkynyl group” may bean unsubstituted alkynyl group or an alkynyl group substituted with atleast one substituent except for a hydrogen atom. The substituent on thealkyl group, alkenyl group, or alkynyl group may be, for example, butnot limited to a deuterium atom.

The present invention also provides an organic electronic device,comprising a first electrode, a second electrode, and an organic layerdisposed between the first electrode and the second electrode. Theorganic layer comprises the composition as described above.

Preferably, the organic electronic device is an organic light emittingdevice (OLED). More preferably, the organic electronic device is a greenorganic electronic device or a red organic electronic device.Preferably, the composition of the present invention may be used as ahost material of EL, especially as a host material for green or redOLEDs, but it is not limited thereto.

Specifically, the organic light emitting device may comprise:

a hole injection layer formed on the first electrode;

a hole transport layer formed on the hole injection layer;

an emission layer formed on the hole transport layer;

an electron transport layer formed on the emission layer;

an electron injection layer formed between the electron transport layerand the second electrode.

In one embodiment, the organic layer may be the emission layer, i.e.,the emission layer comprises a first host material which is thecomposition comprising the first and second host compounds as statedabove.

For example, the emission layer may be a single-layered configuration ora multi-layered configuration. When the emission layer is themulti-layered configuration, e.g., the emission layer comprises a firstemission layer and a second emission layer, the first host material ofthe first emission layer may be made of the single aforesaid compositionand the second host material of the second emission layer may be made ofanother single aforesaid composition or any single conventionalcompound.

Preferably, the emission layer comprises the composition containing thefirst host compound such as Compounds I-1 to I-75 and the second hostcompound such as Compound II-1 to II-48. The OLEDs using the compositionas the host material can reduce the driving voltage and improve thecurrent efficiency.

In another embodiment, the emission layer may further comprise a dopant.

For green OLEDs, the dopant of the emission material is, for example,but not limited to: diaminofluorenes; diaminoanthracenes; ororganometallic compounds of iridium (II) having phenylpyridine ligands.For red OLEDs, the dopant of the emission material is, for example, butnot limited to: organometallic compounds of iridium (II) havingquinoline ligands, isoquinoline ligands, fluoranthene ligands orperiflanthene ligands. With various host materials of the emission layeras stated above, the OLED can emit lights in green or red.

Preferably, the hole injection layer may be a two-layered structure,i.e., the OLED comprises a first hole injection layer and a second holeinjection layer disposed between the first electrode and the holetransport layer.

Said first and second hole injection layers may be made of, for example,but not limited to, polyaniline or polyethylenedioxythiophene.

Preferably, the hole transport layer may be a two-layered structure,i.e., the OLED comprises a first hole transport layer and a second holetransport layer disposed between the two-layered hole injection layerand the emission layer.

Said first and second hole transport layers may be made of, for example,but not limited to:N¹,N^(1′)-(biphenyl-4,4′-diyObis(N¹-(naphthalen-1-yl)-N⁴,N^(4′)-diphenylbenzene-1,4-diamine);or N⁴,N^(4′)-di(naphthalen-1-yl)-N⁴,N^(4′)-diphenylbiphenyl-4,4′-diamine(NPB).

Preferably, the OLED comprises a hole blocking layer formed between theelectron transport layer and the emission layer, to block holes overflowfrom the emission layer to the electron transport layer. Said holeblocking layer may be made of2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) or2,3,5,6-tetramethyl-phenyl-1,4-(bis-phthalimide) (TMPP), but it is notlimited thereto.

Preferably, the OLED comprises an electron blocking layer formed betweenthe hole transport layer and the emission layer, to block electronsoverflow from the emission layer to the hole transport layer. Saidelectron blocking layer may be made of9,9′[1,1′-biphenyl]-4,4′-diylbis-9H-carbazole (CBP) or4,4′,4″-tri(N-carbazolyl)-triphenylamine (TCTA), but it is not limitedthereto.

In the presence of such a hole blocking layer and/or an electronblocking layer in an OLED, the OLED has a higher luminous efficiencycompared to a conventional OLED.

Preferably, the electron transport layer is made of3,3′-[5-[3-(3-Pyridinyl)phenyl][1,1′:3′,1″-terphenyl]-3,3″-diyl]bispyridine(TmPyPb),3-(Biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole(TAZ), tris(2,4,6-trimethyl-3-(pyridin-3-yl)phenyl)borane (3TPYMB),1,3-bis (3,5-dipyrid-3-yl-phenyl)benzene (BmPyPb), or9,10-bis(3-(pyridin-3-yl)phenyl)anthracene (DPyPA), but it is notlimited thereto.

Said electron injection layer may be made of an electron injectionmaterial, for example, but not limited to(8-oxidonaphthalen-1-yl)lithium(II).

Said first electrode is, for example, but not limited to, anindium-doped tin oxide electrode.

Said second electrode has a work function lower than that of the firstelectrode. The second electrode is, for example, but not limited to, analuminum electrode, an indium electrode, or a magnesium electrode.

Other objectives, advantages and novel features of the invention willbecome more apparent from the following detailed description when takenin conjunction with the accompanying drawings.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 illustrates a schematic cross-sectional view of an OLED.

FIG. 2 is a photoluminescence spectra of Compound I-4, Compound II-2 andComposition 16.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

Hereinafter, one skilled in the arts can easily realize the advantagesand effects of a composition for an organic electronic device and anorganic light emitting device using the same in accordance with thepresent invention from the following examples. It should be understoodthat the descriptions proposed herein are just preferable examples onlyfor the purpose of illustrations, not intended to limit the scope of theinvention. Various modifications and variations could be made in orderto practice or apply the present invention without departing from thespirit and scope of the invention.

First Host Compound of a Composition for an Organic Electronic Device

TABLE 1 chemical structures of the first host compounds

Compound I-1

Compound I-2

Compound I-3

Compound I-4

Compound I-5

Compound I-6

Compound I-7

Compound I-8

Compound I-9

Compound I-10

Compound I-11

Compound I-12

Compound I-13

Compound I-14

Compound I-15

Compound I-16

Compound I-17

Compound I-18

Compound I-19

Compound I-20

Compound I-21

Compound I-22

Compound I-23

Compound I-24

Compound I-25

Compound I-26

Compound I-27

Compound I-28

Synthesis of Compounds I-1 to I-15 and I-28 for First Host Compound

Compounds I-1 and I-2 used as the first host compound were synthesizedby the following steps. The synthesis pathway was summarized in SchemeR1.

wherein Intermediate C1 was

and Intermediate C2 was

Compounds I-1 and I-2 could be obtained through a reaction mechanismsame as the synthetic method of Compounds VII and VI in U.S. PatentApplication Publication No. 2017/0213978 A1 by respectively adoptingIntermediate C2 and Intermediate C1 stated above.

Besides, Compound I-7 could be obtained through a reaction mechanismsame as the synthetic method of Compound III in U.S. Patent ApplicationPublication No. 2017/0213978 A1, and the synthetic method was similar toScheme R1 using Intermediate C1 stated above but adopting 4-chloro-2,6-diphenylpyrimidine (CAS No. 29509-91-9) to replace2-chloro-4,6-diphenyl-1,3,5-triazine (CAS No. 3842-55-5).

For Compounds I-3 to I-6, I-8 to I-15 and I-28, they could besuccessfully synthesized through a reaction mechanism similar to SchemeR1 by respectively adopting Intermediate C1 or C2 and other reactantsincluding a triazine or pyrimidine moiety to replace2-chloro-4,6-diphenyl-1,3,5-triazine. The specific reactants including atriazine or pyrimidine moiety and Intermediate C1 or C2 used forsynthesizing Compounds I-3 to I-6, I-8 to I-15 and I-28 were listed inTable 2; besides, Compounds I-3 to I-6, I-8 to I-15 and I-28 wereidentified by FD-MS, and the chemical structure, yield, formula and massof each of Compounds I-3 to I-6, I-8 to I-15 and I-28 were also listedin Table 2-1. Compounds I-3 to I-6, I-8 to I-15 and I-28 were alsoidentified by H¹-NMR and the results thereof were listed in Table 2-2.

Preparation of Reactant for Compound I-10

used to synthesize Compound I-10 was synthesized by the following steps.The synthesis pathway was summarized in Scheme R1-1.

A mixture of dibenzo[b,d]furan-1-ylboronic acid (1.0 eq),2,4-dichloro-6-(D₅)phenyl-1,3,5-triazine (1.1 eq),tris(dibenzylideneacetone)dipalladium[Pd₂(dba)₃] (0.015 eq),triphenylphosphine (PPh₃) were stirred in a mixed solution ofmethoxymethane (DME) (0.5M) and Na₂CO₃ aqueous solution (2.0 M). Thereaction mixture was heated to about 65° C. to 70° C. and stirred for 24hours under nitrogen atmosphere. After completion of the reaction, waterand toluene were added to the reaction mixture. Subsequently, theorganic layer was recovered by solvent extraction operation and driedover sodium sulfate. The solvent was then removed from the organic layerunder reduced pressure, and the resulting residue was washed withmethanol, and dry to obtain a white solid product as

in a yield of 80%. Its FD-MS analysis: C₂₁H₇D₅ClN₃O; and observed valueof 362.82.

TABLE 2-1 Intermediate C1 or C2 and Reactant adopted to prepareCompounds I-3 to I-6, I-8 to I-15 and I-28 and their yields, formulae,and FD-MS data Intermediate First Host Compound C1/ Reactant/ ChemicalYield Formula/ Intermediate C2 CAS No. Structure (%) Mass (M⁺)

83 C₅₂H₃₃N₃/ 699.84

85 C₅₈H₃₇N₃/ 775.93

80 C₅₈H₃₇N₃/ 775.93

86 C₅₂H₃₃N₃/ 699.84

75 C₅₃H₃₄N₂/ 698.85

81 C₅₂H₃₁N₃O/ 713.82

82 C₅₂H₂₆D₅N₃O/ 718.85

81 C₅₈H₃₅N₃O/ 789.92

75 C₅₃H₃₂N₂O/ 712.83

76 C₅₃H₃₂N₂O/ 712.83

70 C₅₃H₃₂N₂O/ 712.83

79 C₅₃H₃₂N₂O/ 712.83

85 C₅₂H₃₁N₃O/ 713.82

TABLE 2-2 H¹-NMR results of Compounds I-3 to I-6, I-8 to I-15 and I-28First Host Compound H¹-NMR

¹H NMR (500 MHz, CDCl₃): δ 9.05 (s, 1H) m 8.79-8.73 (dd, 4H) m 8.43 (dd,1H),7.91 (d 1H), 7.77-7.46 (m, 18H), 7.47 (t, 1H), 7.46-7.30 (m, 2H),7.16 (t, 2H), 7.06 (t, 1H), 6.66 (t, 1H), 5.89 (d, 1H) ppm.

¹H NMR (500 MHz, CDCl₃): δ 8.81 (s, 2H), 8.69 (d, J = 2.0 Hz, 1H), 8.67(d, 1H), 8.64 (d, 2H), 7.90-7.85 (m, 2H), 7.8 g-7.75 (m, 2H), 7.75-7.67(m, 5H), 7.67-7.55 (m, 8H), 7.55-7.50 (m, 4H), 7.50-7.40 (m, 2H),7.40-7.30 (m, 1H), 7.30-7.20 (m, 3H), 7.13 (t, 1H), 7.09 (t, 1H), 6.64(t, 1H), 5.89 (d, 1H) ppm.

¹H NMR (500 MHz, CDCl₃): δ 8.82 (d, 2H), 8.75-8.65 (m, 2H), 8.61 (d,2H), 8.00 (s, 1H), 8.60 (d, 2H), 7.80-7.70 (m, 4H), 7.70-7.61 (m, 6H),7.61-7.51 (m, 7H), 7.51-7.40 (m, 3H), 7.30-7.20 (m, 3H), 7.16 (t, 1H),7.10 (t, 1H), 6.69 (t, 1H), 5.94 (d, J = 10.5 Hz, 1H) ppm.

¹H NMR (500 MHz, CDCl₃): δ 8.94 (s, 1H), 8.75 (d, 4H), 8.73 (d, 1H),8.01 (d, 1H), 7.91 (d, 1H), 7.79 (dd, 1H), 7.72 (dd, 1H), 7.71 (m, 1H),7.63-7.52 (m, 14H), 7.40 (dd, 1H), 7.33 (t, 1H), 7.26 (d, 1H), 7.15-7.07(m, 3H), 6.64 (t, 1H), 5.87 (d, 1H) ppm.

¹H NMR (500 MHz, CDCl₃): δ 9.03 (d, 1H), 8.48-8.41 (m, 1H), 8.39 (dd, J= 13, 1H), 8.30-8.24 (m, 2H), 8.21 (d, 1H), 8.02 (s, 1H), 7.91 (d, 1H),8.03-7.75 (m, 1H), 7.75-7.66 (m, 4H), 7.66-7.58 (m, 6H), 7.58-7.45 (m,7H), 7.45-7.37 (m, 1H), 7.37-7.26 (m, 2H), 7.19-7.10 (m, 2H), 7.10-7.00(m, 1H), 6.67 (t, 1H), 5.93 (d, 1H) ppm.

¹H NMR (500 MHz, CDCl₃): δ 8.74 (s, 1H), 8.63 (d, 1H), 8.58 (d, 2H),8.43 (d, 1H), 8.24 (d, 1H), 7.92 (d, 1H), 7.84 (d, 1H), 7.78 (d, 1H),7.75-7.52 (m, 14H), 7.46 (t, 1H), 7.34 (t, 1H), 7.26 (t, 1H), 7.20-7.05(m, 3H), 6.65 (t, 1H), 5.90 (d, 1H) ppm.

¹H NMR (500 MHz, CDCl₃): δ 8.75 (d, 1H), 8.38 (dd, 1H), 8.46 (d, 1H),8.25 (d, 1H), 7.93 (d, 1H), 7.84 (d, 1H), 7.78 (d, 1H), 7.75-7.60 (m,10H), 7.60-7.53 (m, 1H), 7.52-7.44 (m, 1H), 7.35 (t, 3H), 7.29 (d, J =10.5 Hz, 1H), 7.20-7.05 (m, 3H), 6.70 (t, 1H), 5.92 (d, 1H) ppm.

¹H NMR (500 MHz, CDCl₃): δ 9.04 (s, 1H), 8.93 (s, 1H), 8.88 (s, 1H),8.71 (d, 1H), 8.67 (d, 1H), 8.48 (d, 1H), 8.05-7.85 (m, 3H), 7.84-7.61(m, 7H), 7.60-7.49 (m, 9H), 7.49-7.26 (m, 3H), 7.20-7.11 (m, 2H),7.11-7.00 (m, 1H), 6.68 (t, 1H), 5.92 (d, 1H) ppm.

¹H NMR (500 MHz, CDCl₃): δ 9.01 (d, 1H), 8.49 (d, 1H), 8.39 (dd, , 1H),8.30-8.20 (m, 3H), 8.10-8.03 (m, 2H), 7.98 (d, 1H), 7.90 (d, 1H),7.83-7.73 (m, 1H), 7.72-7.45 (m, 12H), 7.42-7.26 (m, 3H), 7.20-7.10 (m,2H), 7.09-7.00 (m, 1H), 6.65 (td, 1H), 5.90 (d, 1H) ppm.

¹H NMR (500 MHz, CDCl₃): δ 8.66 (d, 2H), 8.39 (s, 1H), 8.20-8.12 (m,2H), 8.09 (d, 1H), 8.05-7.95 (m, 4H), 7.89-7.80 (m, 2H), 7.80-7.69 (m,3H), 7.69-7.58 (m, 6H), 7.57-7.50 (m, 4H), 7.39 (t,, 1H), 7.33 (t, 1H),7.29 (d, 1H), 7.15-7.04 (m, 2H), 6.64 (t, 1H), 5.91 (d, 1H) ppm.

¹H NMR (500 MHz, CDCl₃): δ 8.70(dd, J = 10.0, 3.5 Hz, 2H), 8.58 (d, J =2.5 Hz, 1H), 8.51 (d, 1H), 8.21 (dd, 1H), 8.05 (s, 1H), 8.03-8.01 (m,1H), 8.00-7.93 (m, 2H), 7.92-7.88 (m, 1H), 7.76-7.70 (m, 2H), 7.70-7.56(m, 7H), 7.55-7.45 (m, 5H), 7.4-7.26 (m, 3H), 7.20-7.10 (m, 2H),7.10-7.02 (m, 1H), 6.66 (t, 1H), 5.89 (d, 1H) ppm.

¹H NMR (500 MHz, CDCl₃): δ 8.62-8.52(m, 2H), 8.41 (d, 1H), 8.24 (d, J =2.0 Hz, 1H), 8.20-8.10 (dd, H), 8.04-7.92 (m, 3H), 7.85-7.69 (m, 5H),7.69-7.57 (m, 7H), 7.57-7.45 (m, 4H), 7.45-7.31 (m, 2H), 7.28 (dd, 1H),7.19-7.05 (m, 2H), 6.66 (t, 1H), 5.91 (d, 1H) ppm.

¹H NMR (500 MHz, CDCl₃): δ 9.17 (s, 1H), 8.73-8.68 (m, 2H), 8.65 (d,1H), 8.60 (d, 2H), 8.11 (d, 1H), 8.02 (d, 1H), 7.83 (d, 1H), 7.79-7.69(m, 4H), 7.69-7.61 (m, 6H), 7.61-7.51 (m, 4H), 7.48 (t, 1H), 7.43-7.31(m, 2H), 7.26 (t, 1H), 7.20-7.05 (m, 2H), 6.67 (t, 1H), 5.90 (d, 1H)ppm.

Synthesis of Compounds I-16 to I-19 and I-27 for First Host CompoundCompounds I-16 to I-19 and I-27 used as the first host compound weresynthesized by the following steps. The synthesis pathway was summarizedin Scheme R2.

wherein Intermediate C1′ was

and Intermediate C2′ was

Intermediates C1′ and C2′ could be obtained through a Suzuki-Miyaurareaction from Intermediates D1 and D2 in U.S. Patent ApplicationPublication No. 2017/0213970 A1.

Intermediate C1′ or C2′ (1.0 eq), Reactant Bn (1.2 eq), Pd(OAc)₂ (0.01eq), and 2-(dicyclohexylphosphino)biphenyl[P(Cy)₂(2-biPh)](0.04 eq) werestirred in a mixed solution of toluene/ethanol (0.5M, v/v=10/1) and 3.0M of K₂CO₃ aqueous solution. The reaction mixture was heated to about100° C. and stirred for 12 hours under nitrogen atmosphere. Aftercompletion of the reaction, water and toluene were added to the reactionmixture. Subsequently, the organic layer was recovered by solventextraction operation and dried over sodium sulfate. The solvent was thenremoved under reduced pressure, and the resulting residue was purifiedby silica gel column chromatography. The obtained residue wasrecrystallized with toluene to obtain a white solid product as CompoundsI-16 to I-19 and I-27.

For Compounds I-16 to I-19 and I-27, they could be successfullysynthesized through a reaction mechanism same as Scheme R2 byrespectively adopting Intermediate C1′ or C2′ and other Reactants Bnincluding a triazine or pyrimidine moiety. Intermediate C1′ or C2′ andthe specific Reactants Bn including a triazine or pyrimidine moiety usedfor synthesizing Compounds I-16 to I-19 and I-27 were listed in Table 3;besides, Compounds I-16 to I-19 and I-27 were identified by FD-MS, andthe chemical structure, yield, formula and mass of each of CompoundsI-16 to I-19 and I-27 were also listed in Table 3-1. Compounds I-16 toI-19 and I-27 were also identified by I-1¹-NMR (500 MHz, CDCl₃) and theresults thereof were listed in Table 3-2.

TABLE 3-1 Intermediate C1′ or C2′ and Reactant Bn adopted to prepareCompounds I-16 to I-19 and I-27 and their yields, formulae, and FD-MSdata First Host Compound Intermediate C1′/ Reactant Bn/ Chemical YieldFormula/ Intermediate C2′ CAS No. Structure (%) Mass (M⁺)

85 C₄₆H₂₉N₃/ 623.74

65 C₅₈H₃₇N₃/ 775.93

77 C₅₈H₃₇N₃/ 775.93

82 C₅₈H₃₇N₃/ 775.93

76 C₅₈H₃₇N₃/ 775.93

TABLE 3-2 H¹-NMR results of Compounds I-16 to I-19 and I-27 First HostCompound H¹-NMR

δ 9.01 ppm (d, 1H), 8.99 ppm (s, 1H), 8.75 ppm (d, 4H), 8.65 ppm (d,1H), 8.05 ppm (d, 1H), 7.7 ppm (t, 2H), 7.60-7.58 ppm (m, 8H), 7.35-7.31ppm (m, 4H), 7.29-7.05 ppm (m, 5H), 6.70 ppm (t, 1H), 5.85 ppm (d, 1H).

δ 9.01 ppm (s, 2H), 8.89 ppm (s, 1H), 8.74 ppm (d, 2H), 8.07 ppm (d,1H), 7.84 ppm (dd, 2H), 7.76-7.68 ppm (m, 6H), 7.66-7.57 ppm (m, 6H),,7.52-7.46 ppm (m, 5H) 7.44-7.39 ppm (m, 3H), 7.36-7.30 ppm (m, 4H), 7.16ppm (t, 1H), 7.11-7.06 ppm (m, 2H), 6.70 ppm (t, 1H), 5.89 ppm (d, 1H).

δ 9.23 ppm (s, 1H), 9.08 ppm (s, 2H), 8.96 ppm (d, 1H), 8.92 ppm (s,2H), 8.85 ppm (d, 2H), 8.69 ppm (d, 2H), 8.10 ppm (d, 1H), 8.02 ppm (d,1H), 7.85-7.76 ppm (m, 11H), 7.73-7.67 ppm (m, 10H), 7.64-7.58 ppm (m,12H), 7.53 ppm (dd, 8H), 7.44 ppm (t, 4H), 7.34 ppm (t, 4H), 7.19-7.12ppm (m, 6H), 7.05 ppm (t, 4H), 6.69 ppm (t, 1H), 6.05 ppm (d, 1H), 5.85ppm (d, 1H).

δ 9.23 ppm (s, 1H), 9.04 ppm (s, 2H), 8.94 ppm (d, IH), 8.92 ppm (s,1H), 8.88 ppm (s, 2H), 8.86 ppm (d, 2H), 8.73 ppm (d, 2H) 8.10 ppm (d,1H), 8.19 ppm (s, 1H), 8.02 ppm (d, 1H), 8.00ppm (s, 1H)7.83 ppm (d,6H), 7.78 ppm (d, 4H), 7.70 ppm (dd, 4H), 7.70-7.51 ppm (m, 25H), 7.46ppm (t, 4H), 7.34 ppm (t, 4H), 7.20-7.13 ppm (m, 5H), 7.08-7.04 ppm (m,4H), 6.68 ppm (t, 1H), 6.05 ppm (dd 1H), 5.88 ppm (dd, 1H).

δ 8.97 ppm (s, 3H), 8.84 ppm (s, 1H), 8.81 ppm (d, 1H), 8.77 ppm (d,1H), 8.06 ppm (m, 2H), 7.80-7.76 ppm (m, 6H), 7.62-7.49 ppm (m, 12H),7.47-7.41 ppm (m, 4H), 7.34-7.24 ppm (m, 3H), 7.09-7.05 ppm (m, 2H),6.68 ppm (t, 1H), 5.87 ppm (d, 1H).

Synthesis of Compounds 1-20 to 1-23 for First Host Compound

Compounds I-20 to I-23 used as the first host compound were synthesizedby the following steps. The synthesis pathway was summarized in SchemeR3.

wherein Intermediate Cn-B was

(Intermediate C1-B),

(Intermediate C2-B),

(Intermediate C7-B), or

(Intermediate C3-B).

Compounds I-20 to I-23 could be obtained through a reaction mechanismsame as the synthetic method of Compounds V, IX, XIX and VII in U.S.Patent Application Publication No. 2018/0159044 A1 by respectivelyadopting Intermediate C1-B, Intermediate C2-B, Intermediate C7-B andIntermediate C3-B stated above.

Synthesis of Compounds I-24 to I-26 for First Host Compound

Compounds I-24 and I-25 used as the first host compound were synthesizedby the following steps. The synthesis pathway was summarized in SchemeR4.

wherein Intermediate Dn-B was

(Intermediate D1-B) or

(Intermediate D4-B).

Compounds I-24 and I-25 could be obtained through a reaction mechanismsame as the synthetic method of Compounds VI and VII in U.S. PatentApplication Publication No. 2018/0155312 A1 by respectively adoptingIntermediate D1-B and Intermediate D4-B stated above.

Besides, Compound I-26 could be obtained through a reaction mechanismsame as the synthetic method of Compound III in U.S. Patent ApplicationPublication No. 2018/0155312 A1, and the synthetic method was similar toScheme R4 using Intermediate D1-B stated above but adopting4-chloro-2,6-diphenylpyrimidine to replace2-chloro-4,6-diphenyl-1,3,5-triazine.

Second Host Compound of a Composition for an Organic Electronic Device

TABLE 4 chemical structures and CAS No. of the second host compoundsChemical structure

CAS No. [57102-51-9] [1643479-47-3] Chemical structure

CAS No. [1357150-54-9] [1541194-36-8]

Preparation of a Composition for an Organic Electronic Device

Compositions 1 to 51 were each obtained by adopting an appropriateamount of aforesaid first host compound listed in Table 1 and secondhost compound listed in Table 4, and the species of aforesaid first hostcompound and second host compound used in Compositions 1 to 51 werelisted in Table 5. The weight ratio of the first host compound andsecond host compound in each of Compositions 1 to 47 was 1:1; the weightratio of the first host compound and second host compound inCompositions 48 to 50 was 6:4; the weight ratio of the first hostcompound and second host compound in Composition 51 was 4:6.

Compositions 52 and 53 were respectively obtained by adopting acomposition of TPBi and Compound II-2 or a composition of TPBi andCompound II-1 at a weight ratio of 1:1 as listed in Table 5.

TABLE 5 materials of first and second host compounds and weight ratiotherebetween in Compositions 1 to 53 Weight ratio of first CompositionFirst Host Second Host and second host No. Compound Compound compounds 1Compound I-1 Compound II-1 1:1 2 Compound I-2 Compound II-1 1:1 3Compound I-4 Compound II-1 1:1 4 Compound I-5 Compound II-1 1:1 5Compound I-9 Compound II-1 1:1 6 Compound I-18 Compound II-1 1:1 7Compound I-19 Compound II-1 1:1 8 Compound I-20 Compound II-1 1:1 9Compound I-22 Compound II-1 1:1 10 Compound I-24 Compound II-1 1:1 11Compound I-26 Compound II-1 1:1 12 Compound I-28 Compound II-1 1:1 13Compound I-1 Compound II-2 1:1 14 Compound I-2 Compound II-2 1:1 15Compound I-3 Compound II-2 1:1 16 Compound I-4 Compound II-2 1:1 17Compound I-5 Compound II-2 1:1 18 Compound I-6 Compound II-2 1:1 19Compound I-7 Compound II-2 1:1 20 Compound I-8 Compound II-2 1:1 21Compound I-9 Compound II-2 1:1 22 Compound I-10 Compound II-2 1:1 23Compound I-11 Compound II-2 1:1 24 Compound I-12 Compound II-2 1:1 25Compound I-13 Compound II-2 1:1 26 Compound I-14 Compound II-2 1:1 27Compound I-15 Compound II-2 1:1 28 Compound I-16 Compound II-2 1:1 29Compound I-17 Compound II-2 1:1 30 Compound I-18 Compound II-2 1:1 31Compound I-19 Compound II-2 1:1 32 Compound I-20 Compound II-2 1:1 33Compound I-21 Compound II-2 1:1 34 Compound I-22 Compound II-2 1:1 35Compound I-23 Compound II-2 1:1 36 Compound I-24 Compound II-2 1:1 37Compound I-25 Compound II-2 1:1 38 Compound I-26 Compound II-2 1:1 39Compound I-27 Compound II-2 1:1 40 Compound I-2 Compound II-3 1:1 41Compound I-7 Compound II-3 1:1 42 Compound I-2 Compound II-4 1:1 43Compound I-5 Compound II-4 1:1 44 Compound I-12 Compound II-4 1:1 45Compound I-20 Compound II-4 1:1 46 Compound I-22 Compound II-4 1:1 47Compound I-18 Compound II-4 1:1 48 Compound I-2 Compound II-1 6:4 49Compound I-26 Compound II-1 6:4 50 Compound I-5 Compound II-4 6:4 51Compound I-12 Compound II-4 4:6 52 TPBi Compound II-2 1:1 53 TPBiCompound II-1 1:1

Analysis of Photoluminescence (PL) Spectra

Glass substrates in a thickness of 500 Å cleaned by acetone andisopropyl alcohol were prepared. Compounds I-1 to I-28 listed in Table1, Compounds II-1 to II-4 listed in Table 4 and Compositions 1 to 53listed in Table 5 were deposited on each glass substrate under vacuumdegree of 10⁻⁶ torr to prepare each PL test film of Compounds I-1 toI-28, Compounds II-1 to II-4 and Compositions 1 to 53.

PL test films of Compositions 2, 8, 9, 13, 14, 16, 17, 19, 28 to 39, 42,43, 45 to 47, 52 and the first and second host compounds concerned wererespectively measured by a fluorescence spectrophotometer (HitachiFl-7000) to obtain each set of PL spectra, and then the wavelengths atemission maximum (λ max) thereof in each set of PL spectra weresummarized in Table 6.

The PL spectra of Composition 16 and its components of Compound I-4 andCompound II-2 were measured and recorded as shown in FIG. 2.

TABLE 6 λmax of Compositions 2, 8, 9, 13, 14, 16, 17, 19, 28 to 39, 42,43, 45 to 47 and 52 and λmax of the first and second host compoundsconcerned λmax of λmax of Second λmax of Compo- Second First Host HostCompo- sition First Host Host Compound Compound sition No. CompoundCompound (nm) (nm) (nm) 2 I-2 II-1 393 413 498 8 I-20 II-1 445 413 493 9I-22 II-1 417 413 500 13 I-1 II-2 394 414 488 14 I-2 II-2 393 414 478 16I-4 II-2 407 414 500 17 I-5 II-2 419 414 500 19 I-7 II-2 387 414 462 28I-16 II-2 402 414 478 29 I-17 II-2 404 414 493 30 I-18 II-2 398 414 49431 I-19 II-2 392 414 499 32 I-20 II-2 445 414 466 33 I-21 II-2 401 414488 34 I-22 II-2 417 414 505 35 I-23 II-2 397 414 508 36 I-24 II-2 395414 494 37 I-25 II-2 410 414 483 38 I-26 II-2 389 414 463 39 I-27 II-2403 414 498 42 I-2 II-4 393 388 469 43 I-5 II-4 419 388 469 45 I-20 II-4445 388 472 46 I-22 II-4 417 388 477 47 I-18 II-4 398 388 463 52 TPBiCompound 382 414 418 II-2

As shown in Table 6 and FIG. 2, in each set of PL spectra, the λ max ofCompositions 2, 8, 9, 13, 14, 16, 17, 19, 28 to 39, 42, 43, and 45 to 47were obviously found to red shift to longer wavelength range as comparedwith the λ max of the first host and second host compounds concerned.However, the degree of red shift for λ max of Composition 52 wasobviously smaller than those of Compositions 2, 8, 9, 13, 14, 16, 17,19, 28 to 39, 42, 43, and 45 to 47. Accordingly, it demonstrated thatthe first and second host compounds concerned of Compositions 2, 8, 9,13, 14, 16, 17, 19, 28 to 39, 42, 43 and 45 to 47 respectively formed anexciplex.

Preparation of OLED Devices

A glass substrate coated with an ITO layer (abbreviated as ITOsubstrate) in a thickness of 1500 Å was placed in distilled watercontaining a detergent dissolved therein, and was ultrasonically washed.The detergent was a product manufactured by Fischer Co., and thedistilled water was distilled water filtered twice through a filter(Millipore Co.). After the ITO layer had been washed for 30 minutes, itwas ultrasonically washed twice with distilled water for 10 minutes.After the completion of washing, the glass substrate was ultrasonicallywashed with isopropyl alcohol, acetone and methanol solvents and thendried, after which it was transported to a plasma cleaner. Then thesubstrate was cleaned with oxygen plasma for 5 minutes, and thentransferred to a vacuum evaporator.

After that, various organic materials and metal materials weresequentially deposited on the ITO substrate to obtain the OLED device ofExamples 1 to 43 and Comparative Examples 1 and 2. The vacuum degreeduring the deposition was maintained at 1×10⁻⁶ to 3×10⁻⁷ torr. Herein,the ITO substrate was deposited with a first hole injection layer(HIL-1), a second hole injection layer (HIL-2), a hole transportinglayer (HTL), a green/red emission layer (GEL/REL), an electrontransporting layer (ETL), an electron injection layer (EIL), and acathode (Cthd).

Herein, HI was a material for forming HIL-1 and HIL-2; HI-D was amaterial for forming HIL-1. HT was material for forming HTL; ET wasmaterial for forming ETL. Liq was a material for forming ETL and EIL.Compositions 1 to 53 were respectively a material of GHRH for formingGEL/REL, and GD/RD were respectively a dopant for forming GEL/REL. Themain difference of the OLEDs between the Examples and ComparativeExample was that the GEL/REL of the OLED in the following comparativeexample was made of the Compositions 52 and 53 containing TPBi but theGEL/REL of OLED in the following examples was made of Compositions 1 to51 of the present invention listed in Table 5. The detailed chemicalstructure of foresaid commercial material was listed in Table 7.

TABLE 7 chemical structures of commercial materials for OLED devices

Preparation of Green OLED Devices

To prepare the green OLED device, multiple organic layers wererespectively deposited on the ITO substrate according to the sequence aslisted in Table 8, and the materials and the thicknesses of the organiclayers in green OLED devices were also listed in Table 8.

TABLE 8 coating sequence, materials and thickness of the organic layersin green OLED device Coating Sequence Layer Material Thickness 1 HIL-1HI doped with 3.0 wt % of HI-D  100 Å 2 HIL-2 HI 1400 Å 3 HTL HT  100 Å4 GEL Composition for GH doped with 10.0  400 Å wt % of GD 5 ETL ETdoped with 35.0 wt % of Liq  350 Å 6 EIL Liq   15 Å 7 Cthd Al 1500 Å

Preparation of Red OLED Devices

To prepare the red OLED device, multiple organic layers wererespectively deposited on the ITO substrate according to the sequence aslisted in Table 9, and the materials and the thicknesses of the organiclayers in red OLED devices were also listed in Table 9.

TABLE 9 coating sequence, materials and thickness of the organic layersin red OLED device Coating Sequence Layer Material Thickness 1 HIL-1 HIdoped with 3.0 wt % of HI-D  100 Å 2 HIL-2 HI 2200 Å 3 HTL HT  100 Å 4REL Composition for RH doped with 3.5  300 Å wt % of RD 5 ETL ET dopedwith 35.0 wt % of Liq  350 Å 6 EIL Liq   15 Å 7 Cthd Al 1500 Å

Performance of OLED Devices

1. Color Coordinates (x,y), Driving Voltage and Current Efficiency

To evaluate the performance of OLED devices, the green or red OLEDdevices were measured by PR650 as photometer and Keithley 2400 as powersupply. Color coordinates (x,y) were determined according to the CIEchromaticity scale (Commission Internationale de L'Eclairage, 1931). Theresults were shown in Tables 10 and 11. For the green OLED devices, thedata were collected with a specific luminance at 9000 nits. For the redOLED devices, the data were collected with a specific luminance at 3000nits.

Characteristics of manufactured OLED devices of Examples 1 to 43 andComparative Examples 1 and 2 were measured by the following method.

(1). Measurement of the Current Density Change Depending on VoltageChange

Current values flowing in the devices of the OLEDs were measured, whileincreasing the voltage from 0V to 6.2V by using the power supply, andthe current value of each voltage was measured.

(2). Measurement of the Luminance Change Depending on Voltage Change

Luminance of the manufactured OLEDs was measured by the photometer,while increasing the voltage from 0V to 6.2V by using the power supply.

-   -   (3). Measurement of Current Efficiency

Current efficiency (cd/A) was calculated by using the luminance andcurrent density obtained in aforesaid items (1) and (2).

-   -   (4). Measurement of Color Coordinates (x,y)

Color coordinates (x,y) were determined according to the CIEchromaticity scale. CIE (x,y) changes depended on voltage from 0V to6.2V, which were recorded by the photometer.

Compositions 1 to 4, 6, 8, 9, 11, 15, 18, 20 to 29, 31, 33, 35 to 38, 40to 43, 45 to 51 were respectively used for GH in the GEL of green OLEDsof Examples 1 to 37. Composition 53 was used for GH in the GEL of thegreen OLED of Comparative Example 1. The composition for GH, and data ofCIE, driving voltage and current efficiency of Examples 1 to 37 andComparative Example 1 were listed in Table 10.

TABLE 10 Compositions for GH, CIEs, driving voltages, and currentefficiencies of green OLED devices of Examples 1 to 37 and ComparativeExample 1 Composition Driving Current Example No. CIE voltage efficiencyNo. for GH (x, y) (V) (cd/A) Example 1 1 (0.316, 0.632) 5.24 67.3Example 2 2 (0.319,0.630) 4.18 68.6 Example 3 3 (0.319, 0.629) 4.45 66.6Example 4 4 (0.322, 0.629) 4.72 68.8 Example 5 6 (0.314, 0.632) 5.1861.8 Example 6 8 (0.318, 0.628) 4.60 64.1 Example 7 9 (0.322, 0.628)4.22 62.3 Example 8 11 (0.328, 0.627) 4.74 73.2 Example 9 15 (0.317,0.634) 4.29 71.8 Example 10 18 (0.356, 0.598) 5.41 58.6 Example 11 20(0.314, 0.635) 4.58 63.9 Example 12 21 (0.323, 0.629) 4.14 69.2 Example13 22 (0.330, 0.625) 4.22 70.2 Example 14 23 (0.317, 0.632) 4.62 66.8Example 15 24 (0.314, 0.635) 4.59 70.4 Example 16 25 (0.324, 0.630) 4.6370.7 Example 17 26 (0.313, 0.635) 4.55 70.0 Example 18 27 (0.316, 0.634)4.40 72.3 Example 19 28 (0.318, 0.629) 4.45 65.2 Example 20 29 (0.320,0.627) 4.53 61.5 Example 21 31 (0.317,0.631) 4.55 65.2 Example 22 33(0.315, 0.631) 4.34 62.3 Example 23 35 (0.321, 0.625) 5.75 58.9 Example24 36 (0.318, 0.629) 4.35 66.7 Example 25 37 (0.318, 0.628) 4.14 62.7Example 26 38 (0.312, 0.633) 4.53 65.5 Example 27 40 (0.317, 0.630) 5.2461.0 Example 28 41 (0.317, 0.629) 4.70 59.9 Example 29 42 (0.320, 0.627)4.62 63.0 Example 30 43 (0.322, 0.631) 4.37 72.4 Example 31 45 (0.319,0.627) 4.46 62.9 Example 32 46 (0.322, 0.627) 4.34 63.7 Example 33 47(0.316, 0.630) 5.39 61.8 Example 34 48 (0.323, 0.629) 4.23 68.2 Example35 49 (0.317, 0.633) 4.37 76.1 Example 36 50 (0.331, 0.626) 4.28 73.7Example 37 51 (0.319, 0.633) 4.91 68.1 Comparative 53 (0.313, 0.634)6.30 47.2 Example 1

Compositions 5, 7, 10, 12, 19 and 44 were respectively used for RH inthe REL of red OLEDs of Examples 38 to 43. Composition 53 was used forRH in the REL of the red OLED of Comparative Example 2. The compositionfor RH, and data of CIE, driving voltage and current efficiency ofExamples 38 to 43 and Comparative Example 2 were listed in Table 11.

TABLE 11 Compositions for RH, CIEs, driving voltages, and currentefficiencies of red OLED devices of Examples 38 to 43 and ComparativeExample 2 Driving Current Example Composition CIE voltage efficiency No.No. for RH (x, y) (V) (cd/A) Example 38 5 (0.660, 0.338) 4.05 27.3Example 39 7 (0.665, 0.333) 4.31 27.0 Example 40 10 (0.660, 0.338) 4.3128.7 Example 41 12 (0.661, 0.337) 4.40 26.0 Example 42 19 (0.661, 0.336)4.74 28.7 Example 43 44 (0.661, 0.336) 4.53 28.2 Comparative 53 (0.658,0.339) 5.80 17.5 Example 2

2. Measurement of Lifespan (T95)

Lifespan (T95) was measured by OLED life time test system (Chroma model58131). T95 represents lifespan data evaluating a period taken forluminance to reach 95% with respect to the initial luminance (at 7,000nits for green OLEDs and at 6000 nits for red OEDs).

The composition for GH and the lifespan of Examples 1 to 7, 12, 13, 18,29 to 34, 36 and 37 and Comparative Example 1 were listed in Table 12.

TABLE 12 Compositions for GH and lifespan of green OLED devices ofExamples 1 to 7, 12, 13, 18, 29 to 34, 36 and 37 and Comparative Example1 Example Composition Lifespan (T95) No. No. (hrs) Example 1 1 90Example 2 2 104 Example 3 3 47 Example 4 4 81 Example 5 6 65 Example 6 861 Example 7 9 112 Example 12 21 40 Example 13 22 20 Example 18 27 44Example 29 42 112 Example 30 43 30 Example 31 45 87 Example 32 46 98Example 33 47 56 Example 34 48 52 Example 36 50 68 Example 37 51 20Comparative Example 1 53 1

The composition for RH and the lifespan of Examples 38, 39, 41 and 43and Comparative Example 1 were listed in Table 13.

TABLE 13 Compositions for RH and lifespan of red OLED devices ofExamples 38, 39, 41 and 43 and Comparative Example 2 Example CompositionLifespan (T95) No. No. (hrs) Example 38 5 32 Example 39 7 17 Example 4112 16 Example 43 44 14 Comparative Example 2 53 0.5

Based on the results, in comparison with the Composition 53 containingthe commercial host material for the green emission layer, adoptingCompositions 1 to 4, 6, 8, 9, 11, 15, 18, 20 to 29, 31, 33, 35 to 38, 40to 43, 45 to 51 of the present invention as the host material for thegreen emission layer can reduced the driving voltage and improve thecurrent efficiency of the green OLEDs. Similarly, in comparison with theComposition 53 containing the commercial host material for the redemission layer, adopting Compositions 5, 7, 10, 12, 19 and 44 of thepresent invention as the host material for the red emission layer alsocan reduce the driving voltage and improve the current efficiency of thered OLEDs.

Even more, adopting Compositions 1 to 4, 6, 8, 9, 21, 22, 27, 42, 43, 45to 48, 50 and 51 of the present invention as the host material for thegreen emission layer can prolong the lifespan of the green OLEDs.Similarly, adopting Compositions 5, 7, 12 and 44 of the presentinvention as the host material for the red emission layer can prolongthe lifespan of the red OLEDs.

The reason is that the specific first host compounds had a suitablelowest unoccupied molecular orbital (LUMO) level for the better electroninjection to the EL compared to TPBi of Comparative example, leading tothe lower driving voltage. In addition, the cooperation of the specificfirst and second host compounds would respectively form an exciplex asshown in Table 6, and such emission mechanism can effectively use theexciton to lead the high efficiency devices.

It demonstrated that the composition of the present invention issuitable as a host material for any green or red OLEDs, and allows theOLEDs using the same to have low driving voltage and improved currentefficiency, and even prolonged lifespan.

Even though numerous characteristics and advantages of the presentinvention have been set forth in the foregoing description, togetherwith details of the structure and features of the invention, thedisclosure is illustrative only. Changes may be made in the details,especially in matters of shape, size, and arrangement of parts withinthe principles of the invention to the full extent indicated by thebroad general meaning of the terms in which the appended claims areexpressed.

What is claimed is:
 1. A composition for an organic electronic device,comprising: a first host compound represented by the following Formula(I); and

a second host compound represented by the following Formula (II);

wherein Y in Formula (I) is a single bond, an oxygen atom or a sulfuratom; Z¹ to Z³ in Formula (I) are each independently CH, adjacent two ofZ¹ to Z³ in Formula (I) are joined together to form an aryl ring and aremaining one of Z¹ to Z³ is CH, or adjacent two of Z¹ to Z³ in Formula(I) are joined together to form a heteroaryl ring containing at leastone furan group or at least one thiophene group and the remaining one ofZ¹ to Z³ is CH; two of X¹ to X³ in Formula (I) are each independently anitrogen atom, and the other of X¹ to X³ in Formula (I) is CH or anitrogen atom; L′, L¹ and L² in Formula (I) are each independently anarylene group having 6 to 18 ring carbon atoms; n′, n1 and n2 are eachindependently an integer from 0 to 2; G¹ and G² in Formula (I) are eachindependently an aryl group having 6 to 18 ring carbon atoms, an aryloxygroup having 6 to 18 ring carbon atoms, an arylthioxy group having 6 to18 ring carbon atoms, or a heteroaryl group containing a N, O, or S atomand having 3 to 30 ring carbon atoms; L³ in Formula (II) is an arylenegroup having 6 to 18 ring carbon atoms; n3 is an integer from 0 to 2; G⁴and G⁵ in Formula (II) are each independently an aryl group having 6 to18 ring carbon atoms, an aryloxy group having 6 to 18 ring carbon atoms,an arylthioxy group having 6 to 18 ring carbon atoms, or an heteroarylgroup containing a N, O, or S atom and having 3 to 30 ring carbon atoms;and Q¹ and Q² in Formula (II) are each independently CH or Q¹ and Q² inFormula (II) are joined together to form an aryl ring.
 2. Thecomposition as claimed in claim 1, wherein the first host compound isrepresented by the following Formula (I′):


3. The composition as claimed in claim 2, wherein a weight ratio of thefirst and second host compounds ranges from 3:7 to 7:3.
 4. Thecomposition as claimed in claim 2, wherein the first host compound isrepresented by any one of the following Formulae (I-I) to (I-XVI):


5. The composition as claimed in claim 2, wherein the second hostcompound is represented by any one of the following Formulae (II-I) to(II-III):

wherein W¹ and W² are each independently a methyl group, an ethyl group,a propyl group, a butyl group or a phenyl group.
 6. The composition asclaimed in claim 2, wherein L¹ and L² are each independently a phenylenegroup.
 7. The composition as claimed in claim 2, wherein n1 and n2 areeach independently an integer 0 or
 1. 8. The composition as claimed inclaim 2, wherein G¹ and G² are each independently selected from thegroup consisting of: a phenyl group, a naphthyl group and a3,5-diphenylphenyl group.
 9. The composition as claimed in claim 2,wherein G¹ and G² are each independently selected from the groupconsisting of:

where X is O, S, or

wherein p is an integer from 1 to 5, m is an integer from 1 to 4, and nis an integer from 1 to 3; and A¹ to A³ are each independently selectedfrom the group consisting of: a hydrogen atom, a deuterium atom, a halogroup, a cyano group, a nitro group, an alkyl group having 1 to 6 carbonatoms, an alkenyl group having 2 to 6 carbon atoms, and an alkynyl grouphaving 2 to 6 carbon atoms.
 10. The composition as claimed in claim 2,wherein L³ is a phenylene group.
 11. The composition as claimed in claim2, wherein n3 is an integer 0 or
 1. 12. The composition as claimed inclaim 2, wherein G⁴ and G⁵ are each independently selected from thegroup consisting of: a phenyl group, a biphenylyl group, and a naphthylgroup.
 13. The composition as claimed in claim 2, wherein G⁴ and G⁵ areeach independently selected from the group consisting of:

where X′ is O, S, or

wherein p′ is an integer from 1 to 5, m′ is an integer from 1 to 4, andn′ is an integer from 1 to 3; and A⁴ to A⁶ are each independentlyselected from the group consisting of: a hydrogen atom, a deuteriumatom, a halo group, a cyano group, a nitro group, an alkyl group having1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, and analkynyl group having 2 to 6 carbon atoms.
 14. The composition as claimedin claim 2, wherein a group of

of the first host compound represented by Formula (I′) is selected fromthe group consisting of:


15. The composition as claimed in claim 2, wherein G⁴ and G⁵ are eachindependently selected from the group consisting of:


16. The composition as claimed in claim 1, wherein the first hostcompound is selected from the group consisting of:


17. The composition as claimed in claim 16, wherein the second hostcompound is selected from the group consisting of:


18. An organic electronic device, comprising a first electrode, a secondelectrode, and an organic layer disposed between the first electrode andthe second electrode, wherein the organic layer comprises thecomposition as claimed in claim
 1. 19. The organic electronic device asclaimed in claim 18, wherein the organic electronic device is an organiclight emitting device.
 20. The organic electronic device as claimed inclaim 19, wherein the organic light emitting device comprises: a holeinjection layer formed on the first electrode; a hole transport layerformed on the hole injection layer; an emission layer formed on the holetransport layer, wherein the emission layer comprises the composition asclaimed in claim 1; an electron transport layer formed on the emissionlayer; and an electron injection layer formed between the electrontransport layer and the second electrode.